Acta Chimica Sinica ›› 2009, Vol. 67 ›› Issue (23): 2732-2738. Previous Articles     Next Articles

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C(3)-酯基取代的1,5-苯并硫氮杂卓的合成、晶体结构及抑菌和构效关系的研究

李文红c,兰佳明b,李成a,曹云涛a,王海波a,王兰芝a,张萍a,王永祥*,b,李 媛*,a   

  1. (a河北师范大学化学与材料科学学院 石家庄 050016) (b河北医科大学病原生物学部 石家庄 050017) (c河北工业职业技术学院环境与化学工程系 石家庄 050091)
  • 收稿日期:2009-05-01 修回日期:2009-07-21 出版日期:2009-12-14 发布日期:2009-08-10
  • 通讯作者: 李媛 E-mail:yuanli@mail.hebtu.edu.cn

Synthesis, Crystal Structure, Antimicrobial Activity and Structure Activity Relationship of 3-Ethoxycarbonyl-1,5-benzothiazepines

Li, Wenhongc,Lan, Jiamingb,Li, Chenga,Cao, Yuntaoa,Wang, Haiboa ,Wang, Lanzhia,Zhang, Pinga,Wang, Yongxiang*,b,Li, Yuan*,a   

  1. (a College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016) (b Department of Pathogenic Biology, Hebei Medical University, Shijiazhuang 050017) (c Environment and Chemical Engineering, Heibei College of Industry and Technology, Shijiazhuang 050091)
  • Received:2009-05-01 Revised:2009-07-21 Online:2009-12-14 Published:2009-08-10

Three kinds of 3-ethoxycarbonyl-1,5-benzothiazepines were designed, synthesized and structurally confirmed by elemental analysis, IR, 1H NMR, MS and X-ray diffraction. The crystal of compound 5b belongs to monoclinic, space group C2/c with unit cell dimensions a=2.0319(4) nm, b=1.4985(3) nm, c=1.3659(3) nm, α=90°, β=120.49(3)°, γ=90°, V=3.5840(12) nm3, Z=8, Dc=1.397 g/cm3, μ=0.351 mm-1, F(000)=1560, R=0.0478, and Rw=0.1304. Studies on the synthesis conditions of 2,3/2,5-dihydro-1,5-benzothiazepines revealed that 2,3/2,5-dihydro-1,5-benzothiazepines that are imine-enamine tautomers were speed control and balance control products respectively. The biological evaluation of those compounds showed that 1,5-benzothiazepines with C=N group had moderate to excellent antimicrobial activities and the C=N double bond in the newly synthesized compounds was the key function group for their antifungal activities.

Key words: 1,5-benzothiazepine, speed control product, balance control product, antibacterial activity, structure-activity relationship